US8765851B2 - Free radical initiator modified hot melt adhesive composition including functionalized polyethylene and propylene-alpha-olefin polymer - Google Patents
Free radical initiator modified hot melt adhesive composition including functionalized polyethylene and propylene-alpha-olefin polymer Download PDFInfo
- Publication number
- US8765851B2 US8765851B2 US13/529,269 US201213529269A US8765851B2 US 8765851 B2 US8765851 B2 US 8765851B2 US 201213529269 A US201213529269 A US 201213529269A US 8765851 B2 US8765851 B2 US 8765851B2
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- US
- United States
- Prior art keywords
- adhesive composition
- weight
- wax
- propylene
- polyethylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/10—Homopolymers or copolymers of propene
- C09J123/14—Copolymers of propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/06—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
TABLE 1 | |||||||||||
A-C-X | |||||||||||
1783 | EPOLENE | ||||||||||
Polymer | Wax1 | N21 Wax2 | A-C | Peroxide | |||||||
Polymer | (% by | (% by | (% by | 597 | (% by | ||||||
Sample | No. | weight) | weight) | weight) | Wax3 | weight) | Mz | Mn | Mw | Mz/Mn | Mz/Mw |
Base 1 | 1 | 85 | 15 | 0 | 0 | 1.7 | 47600 | 1620 | 17800 | 29.4 | 2.7 |
Base 2 | 1 | 95 | 5 | 0 | 0 | 1.7 | 56200 | 1830 | 19900 | 30.7 | 2.8 |
Base 3 | 1 | 95 | 0 | 5 | 0 | 1.7 | ND | ND | ND | ND | ND |
Base 4 | 1 | 95 | 0 | 0 | 5 | 1.7 | ND | ND | ND | ND | ND |
Base 5 | 1 | 95 | 5 | 0 | 0 | 1.1 | ND | ND | ND | ND | ND |
Base 6 | 2 | 95 | 5 | 0 | 0 | 1.7 | ND | ND | ND | ND | ND |
Base 7 | 3 | 90 | 10 | 0 | 0 | 1.7 | ND | ND | ND | ND | ND |
Base 8 | 4 | 85 | 15 | 0 | 0 | 1.7 | ND | ND | ND | ND | ND |
Base 8a | 3 | 85 | 15 | 0 | 0 | 1.7 | ND | ND | ND | ND | ND |
Base 9 | 1 | 100 | 0 | 0 | 0 | 1.5 | ND | ND | ND | ND | ND |
Base 10 | 2 | 100 | 0 | 0 | 0 | 1.7 | ND | ND | ND | ND | ND |
Base 11 | 5 | 85 | 15 | 0 | 0 | 1.7 | ND | ND | ND | ND | ND |
Base 12 | 2 | 95 | 5 | 0 | 0 | 1.1 | 46300 | 2280 | 19300 | 20.3 | 2.5 |
1= A-C-X 1783 maleated linear low density polyethylene wax having an acid number of 4.5, a saponification value of 6.2, a viscosity at 140° C. of 60 centipoise, a penetration value of 0.5 dmm, a Mw of 8,650, a Mn of 1,700, an Mz of 18,000 and a Mw/Mn of 5.08. | |||||||||||
2= EPOLENE N21 polyethylene wax | |||||||||||
3= A-C 597 maleated polypropylene wax | |||||||||||
ND = Not Determined |
Controls 1-4
TABLE 2 | ||||||||||
Base % | ||||||||||
by | ||||||||||
Sample | Base No. | weight | Wax4 | Wax5 | Wax6 | Wax10 | Polymer | Tg (° C.) | Tm (° C.) | Acid No. |
Example 1 | Base 2 | 90 | 7 | 1 | 0 | 0 | 27 | −24 | 116 | 1.0 |
Example 2 | Base 1 | 100 | 0 | 0 | 0 | 0 | 0 | ND | ND | ND |
Example 3 | Base 2 | 90 | 10 | 0 | 0 | 0 | 0 | −27 | 116 | 0.1 |
Example 4 | Base 5 | 90 | 8.5 | 1.5 | 0 | 0 | 0 | ND | ND | ND |
Example 5 | Base 5 | 82 | 7 | 2 | 0 | 0 | 98 | −22 | 117 | ND |
Example 6 | Base 8 | 100 | 0 | 0 | 0 | 0 | 0 | ND | ND | ND |
Example 7 | Base 8a | 100 | 0 | 0 | 0 | 0 | 0 | −24 | 110 | 0.3 |
Example 8 | Base 11 | 100 | 0 | 0 | 15 | 0 | 0 | −27 | 110 | 0.3 |
Example 9 | Base 2 | 90 | 7 | 0 | 0 | 0 | 39 | −21 | 113 | 0.5 |
Example 10 | Base 5 | 90 | 8.5 | 1.5 | 0 | 0 | 0 | ND | ND | ND |
Example 11 | Base 5 | 90 | 7 | 1.5 | 0 | 0 | 1.57 | ND | ND | ND |
Example 12 | Base 5 | 90 | 7 | 1.5 | 0 | 0 | 1.59 | ND | ND | ND |
Example 13 | Base 11 | 87 | 8.5 | 1 | 0 | 0 | 211 | ND | ND | ND |
Example 14 | Base 11 | 87 | 8.5 | 0 | 0 | 1 | 211 | ND | ND | ND |
Control 1 | Base 10 | 85 | 0 | 0 | 15 | 0 | 0 | ND | ND | ND |
Example 15 | Base 6 | 100 | 0 | 0 | 0 | 0 | 0 | −24 | 116 | 0.1 |
Example 16 | Base 7 | 100 | 0 | 0 | 0 | 0 | 0 | −25 | 113 | 0.1 |
Control 2 | Base 9 | 76.5 | 20 | 2 | 0 | 0 | 0 | ND | ND | ND |
Example 17 | Base 8 | 100 | 0 | 0 | 0 | 0 | 0 | ND | ND | ND |
Example 18 | Base 10 | 85 | 0 | 0 | 15 | 0 | 0 | −25 | 153 | 1.3 |
−17 | 111 | |||||||||
Control 3 | Base 3 | 90 | 0 | 0 | 10 | 0 | 0 | −25 | 114 | 0.8 |
Control 4 | Base 4 | 90 | 10 | 0 | 0 | 0 | 0 | ND | ND | ND |
FT = fiber tear | ||||||||||
4= EPOLENE N21 polyethylene wax (Westlake Chemical Corp., Houston, Texas) | ||||||||||
5= A-C 597 maleated polypropylene wax | ||||||||||
6= A-C 1783 maleated polyethylene wax | ||||||||||
7= EPOLENE C-10 polyethylene (Westlake Chemical Corp., Houston, Texas) | ||||||||||
8= REXTAC RT 2115 propylene homopolymer (Rextac LLC, Odessa, Texas) | ||||||||||
9= EPOLENE C-18 maleated branched polyethylene (Westlake Chemical Corp., Houston, Texas) | ||||||||||
10= A-C 1325 maleated polypropylene wax (Honeywell International Inc., Morristown, New Jersey). | ||||||||||
11= VERSIFY 4200 metallocene propylene-ethylene copolymer (Dow Chemical, Midland, Michigan) |
TABLE 3 | ||||||||||
Gardner | ||||||||||
Gardner | Gardner | Color | ||||||||
% FT | % FT | % FT | Viscosity | Color | Color (48 | (96 | Set Time | Clarity | Clarity | |
Sample | −29° C. | 22° C. | +60° C. | (cP) | (initial) | Hours) | Hours) | (seconds) | (Initial) | (96 hours) |
Example 1 | 76 | 100 | 80 | 750 | 2-3 | 5 | 5-6 | 14 | Slightly | Slightly |
Cloudy | Cloudy | |||||||||
Example 2 | 91 | 100 | 89 | 823 | 1 | 3 | 5 | 14 | Light, | Light, |
clear | clear | |||||||||
Example 3 | 48 | 100 | 60 | 750 | 1 | 2 | 4 | 7 | Hazy, light | Hazy, light |
Example 4 | 85 | 100 | 95 | 825 | 1-2 | 2-3 | 6 | 8 | Clear | Some |
Settling | ||||||||||
Example 5 | 75 | 100 | 70 | 1175 | 2 | 4 | 5-6 | 5 | Hazy | Hazy |
Example 6 | 86 | 100 | 94 | 1100 | 2 | 5 | 6 at 72 | 19 | Hazy | Hazy |
hours | ||||||||||
Example 7 | 85 | 100 | 93 | 1125 | 1 | 5 | 5-6 at | 28 | Hazy | Hazy at 72 |
72 hours | hours | |||||||||
Example 8 | 80 | 100 | 95 | 1062 | 1 | 2 | 6 | 7 | Clear | ND |
Example 9 | 54 | 100 | 43 | 765 | 2 | 4 | 5 | 13 | Slightly | Slightly |
Cloudy | Cloudy | |||||||||
Example 10 | 75 | 100 | 95 | 825 | 1-2 | 2-3 | 6 | 8 | Clear | Some |
Settling | ||||||||||
Example 11 | 75 | 100 | 65 | 810 | 1 | ND | ND | 7 | Hazy | ND |
Example 12 | 70 | 100 | 85 | 762 | 1 | 2-3 | ND | 5 | Hazy | Settling |
Example 13 | 80 | 100 | 60 | 1305 | 2 | 3 | 6 | 5 | Cloudy | Some |
settling | ||||||||||
Example 14 | 60 | 100 | 40 | 1184 | 1 | 2 | 4 | 5 | Cloudy | cloudy |
Control 1 | 15 | 70 | 50 | ND | ND | ND | ND | >5 | Cloudy | ND |
Example 15 | 75 | 100 | 0 | 1362 | 1-2 | 4 | 6 | 6 | Cloudy | Cloudy |
Example 16 | 90 | 100 | 5 | 1337 | 1-2 | 4 | 5 | 6 | Cloudy | Cloudy |
Control 2 | 10 | 100 | 100 | 1300 | 4-5 | 6 | 7 | 11 | Cloudy | Particles |
Example 17 | 50 | 100 | 10 | 2125 | 1-2 | 4 | 5 | 7 | Cloudy | Cloudy |
Example 18 | 64 | 100 | 80 | 1908 | 2 | 5 | ND | 8 | Cloudy | Phase |
Separation. | ||||||||||
Settling | ||||||||||
Control 3 | 21 | 100 | 85 | 1000 | 2 | 3 | ND | 12 | Cloudy | Seeded out |
within 48 | ||||||||||
hours | ||||||||||
Control 4 | 83 | 100 | 80 | 1227 | 6 | ND | 7 at 72 | 30 | Cloudy | Gelled. |
hours | Settled out | |||||||||
*= ND = Not Determined |
Claims (42)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US13/529,269 US8765851B2 (en) | 2011-06-27 | 2012-06-21 | Free radical initiator modified hot melt adhesive composition including functionalized polyethylene and propylene-alpha-olefin polymer |
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US201161501585P | 2011-06-27 | 2011-06-27 | |
US13/529,269 US8765851B2 (en) | 2011-06-27 | 2012-06-21 | Free radical initiator modified hot melt adhesive composition including functionalized polyethylene and propylene-alpha-olefin polymer |
Publications (2)
Publication Number | Publication Date |
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US20120329929A1 US20120329929A1 (en) | 2012-12-27 |
US8765851B2 true US8765851B2 (en) | 2014-07-01 |
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US13/529,269 Expired - Fee Related US8765851B2 (en) | 2011-06-27 | 2012-06-21 | Free radical initiator modified hot melt adhesive composition including functionalized polyethylene and propylene-alpha-olefin polymer |
Country Status (6)
Country | Link |
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US (1) | US8765851B2 (en) |
EP (1) | EP2723825B1 (en) |
CN (1) | CN103649258B (en) |
BR (1) | BR112013033143A2 (en) |
MX (1) | MX339901B (en) |
WO (1) | WO2013003197A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20210324239A1 (en) * | 2018-09-06 | 2021-10-21 | Evonik Operations Gmbh | Amorphous poly-alpha-olefins and use thereof in hot-melt compositions having improved sprayability |
Families Citing this family (13)
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US9593235B2 (en) | 2013-02-15 | 2017-03-14 | H.B. Fuller Company | Reaction product of propylene polymer and wax, graft copolymers derived from polypropylene polymer and wax, hot melt adhesive compositions including the same, and methods of using and making the same |
US9267060B2 (en) | 2013-02-15 | 2016-02-23 | H.B. Fuller Company | Reaction product of propylene polymer and wax, graft copolymers derived from polypropylene polymer and wax, hot melt adhesive compositions including the same, and methods of using and making the same |
WO2014127093A1 (en) * | 2013-02-15 | 2014-08-21 | H.B. Fuller Company | Reaction product of propylene polymer and wax, graft copolymers derived from polypropylene polymer and wax, hot melt adhesive compositions including the same, and methods of using and making the same |
WO2014152692A1 (en) * | 2013-03-15 | 2014-09-25 | Braskem America, Inc. | Propylene polymer resins |
CN103289628B (en) * | 2013-06-24 | 2014-08-13 | 苏州新区佳合塑胶有限公司 | Polyethylene hot melt adhesive used for sheet materials and preparation method thereof |
EP3058043B1 (en) | 2013-10-18 | 2021-07-14 | ExxonMobil Chemical Patents Inc. | High polymer load polyolefin adhesive compositions |
US10336921B2 (en) | 2014-04-22 | 2019-07-02 | Exxonmobil Chemical Patents Inc. | Adhesive compositions for nonwoven applications |
US10023771B2 (en) | 2014-08-21 | 2018-07-17 | Dow Global Technologies Llc | Hot melt adhesive composition |
WO2016026121A1 (en) * | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Adhesive compositions comprising low molecular weight functionalized olefin-based polymers |
CA3010859A1 (en) * | 2016-01-13 | 2017-07-20 | Equistar Chemicals, Lp | Polyolefin-based compositions, adhesives, and related multi-layered structures prepared therefrom |
JP6843890B2 (en) * | 2016-06-03 | 2021-03-17 | ダウ グローバル テクノロジーズ エルエルシー | Adhesive composition |
EP3625297A4 (en) * | 2017-05-19 | 2021-03-17 | Honeywell International Inc. | Compositions including copolymer formulations for improving adhesion to low surface energy substrates |
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2012
- 2012-06-21 CN CN201280031600.3A patent/CN103649258B/en not_active Expired - Fee Related
- 2012-06-21 US US13/529,269 patent/US8765851B2/en not_active Expired - Fee Related
- 2012-06-21 EP EP12733326.8A patent/EP2723825B1/en not_active Not-in-force
- 2012-06-21 BR BR112013033143A patent/BR112013033143A2/en not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
---|---|
BR112013033143A2 (en) | 2017-01-24 |
CN103649258A (en) | 2014-03-19 |
MX2013015169A (en) | 2014-03-31 |
CN103649258B (en) | 2016-07-06 |
WO2013003197A1 (en) | 2013-01-03 |
US20120329929A1 (en) | 2012-12-27 |
EP2723825A1 (en) | 2014-04-30 |
EP2723825B1 (en) | 2015-08-26 |
MX339901B (en) | 2016-06-16 |
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